NP-MRD: Showing NP-Card for 1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione (NP0220263)

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Record Information

Version

2.0

Created at

2022-09-05 21:31:34 UTC

Updated at

2022-09-05 21:31:34 UTC

NP-MRD ID

NP0220263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione

Description

SCHEMBL16227094 belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. 1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione is found in Cratoxylum formosum. Based on a literature review very few articles have been published on SCHEMBL16227094.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223312D          

 31 33  0  0  0  0            999 V2000
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1612   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END


  Mrv1652309052223312D          

 31 33  0  0  0  0            999 V2000
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1612   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(C\C=C\C(C)(C)O)=C/COC1=CC(O)=C2C(=O)C3=C(O)C=C(C)C=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O6/c1-14(6-5-8-25(3,4)30)7-9-31-16-12-18-22(20(27)13-16)24(29)21-17(23(18)28)10-15(2)11-19(21)26/h5,7-8,10-13,26-27,30H,6,9H2,1-4H3/b8-5+,14-7+

> <INCHI_KEY>
FAUQLQYXYZFMJO-MNJDMZAHSA-N

> <FORMULA>
C25H26O6

> <MOLECULAR_WEIGHT>
422.477

> <EXACT_MASS>
422.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.35424872564499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,8-dihydroxy-3-{[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methyl-9,10-dihydroanthracene-9,10-dione

> <JCHEM_LOGP>
5.716736519333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.557328421201944

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.887587237574536

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5476550340731987

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
121.48669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1,8-dihydroxy-3-{[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.774  -5.954   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.234  -3.286   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    6                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   10   24                                                  
CONECT   24   23                                                            
CONECT   25    2   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₆

Average Mass

422.4770 Da

Monoisotopic Mass

422.17294 Da

IUPAC Name

1,8-dihydroxy-3-{[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,8-dihydroxy-3-{[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

C\C(C\C=C\C(C)(C)O)=C/COC1=CC(O)=C2C(=O)C3=C(O)C=C(C)C=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C25H26O6/c1-14(6-5-8-25(3,4)30)7-9-31-16-12-18-22(20(27)13-16)24(29)21-17(23(18)28)10-15(2)11-19(21)26/h5,7-8,10-13,26-27,30H,6,9H2,1-4H3/b8-5+,14-7+

InChI Key

FAUQLQYXYZFMJO-MNJDMZAHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cratoxylum formosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Aryl ketone
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Vinylogous acid
Tertiary alcohol
Ketone
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.72	ChemAxon
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.49 m³·mol⁻¹	ChemAxon
Polarizability	46.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17243965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16085298

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione (NP0220263)

MOL for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

3D MOL for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

3D SDF for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

3D-SDF for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

PDB for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

3D PDB for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

SMILES for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

INCHI for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

Structure for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)

3D Structure for NP0220263 (1,8-dihydroxy-3-{[(2e,5e)-7-hydroxy-3,7-dimethylocta-2,5-dien-1-yl]oxy}-6-methylanthracene-9,10-dione)